Photoinduced Electron Transfer Switching Mechanism of a Naphthalimide Derivative with its Solvatochromic Behaviour: An Experimental and Theoretical Study with In Cell Investigations

Abstract

The sole existence of a t-bone-shaped naphthalimide derivative [2-(2-aminoethyl)-1H-benzo[de]isoquinoline-1,3(2H)dione] (NAP), which gives rise to a photoinduced electron transfer (PET) mechanism, has been established using a combination of experimental and theoretical studies. In parallel an in vitro-in cell PET mechanism has also been shown. To understand the photophysics of NAP, solvent studies have been carried out in different solvents. In addition, theoretical calculations have been conducted to explain the spectroscopic properties through optimized structures. A "turn off" PET mechanism has also been observed in the presence of specific metal ions, namely, Cr , Fe and Hg among a series of metal ions. Theoretical studies reveal that NAP-Cr , NAP-Fe and NAP-Hg have their HOMO energy states lying in between a HOMO-LUMO energy state of the t-bone-type NAP molecule. On the contrary, the HOMO state of the other metal ion-NAP conjugate (NAP-M ) does not lie in between the HOMO-LUMO energy gap of the t-bone-type NAP molecule. Coupled with in vitro studies, in cell investigations reveal an enhancement of fluorescence intensity of NAP upon cytosolic metal sensing. Furthermore, a very high cell viability of NAP treated cells as tested by MTT assay and a fast permeation of the said compound as revealed by flow cytometry suggest NAP to be a potential candidate in metal sensing and bioimaging applications.

Realization of multi-configurable logic gate behaviour on fluorescence switching signalling of naphthalene diimide congeners

“…36 Similarly, Singharoy et al, and Yang et al, with the help of naphthalimide as precursor, have demonstrated the combinational logic gate behaviour along with their different applications. 37,38 In view of the competitive advantages mentioned above, we have demonstrated a uorescence switching phenomenon of NDI probes in response to the external stimuli and realized their behaviour in binary format to implement in digital logic gates. The novelty of the presented work lies in achieving the modulation of uorescent ON/OFF switching using NDI congeners concerning the use of external stimuli.…”

“…36 Similarly, Singharoy et al , and Yang et al , with the help of naphthalimide as precursor, have demonstrated the combinational logic gate behaviour along with their different applications. 37,38 …”

Nonionic Surfactants as Potential Carriers of a Synthesized Pyrimidine Derivative: Spectroscopic and Quantum Chemical Investigations

“…To get better results, we optimized the ground and excited state geometries of ANHP by DFT/6‐311G and CIS/6‐311G methods, respectively. We then calculated the absorption and emission spectra of ANHP using the TD‐DFT method with the B3LYP exchange‐correlation functional. The results of theoretical calculations corresponded to the experimental observations.…”

Thiourea Modified Doxorubicin: A Perspective pH-Sensitive Prodrug

“…For The results of stationary fluorescence and fluorescence kinetics analysis are shown in Figure 5 and Figure S4. Fluorescence kinetics (Figure S4) analysis allowed for the calculation of the contribution of an exponent with a characteristic time of 6.0 ns corresponding to free naphthalimide−which was 52% (calculated from the known values 36 of the pre-exponential factors = 619 /(619 + 561) = 0.52), i.e. there is an increase in contribution of this component if compared to neutral pH, where it was 37%.…”